After meeting at Vanderbilt University where both were psychology majors, Darren Richard and Charles Kim began playing together in 1990. They backed a female jazz vocalist in Nashville-area clubs before moving to Chicago and forming Pinetop Seven in 1994. A year later, they recorded their eponymous debut in their landlord's attic. Shortly after, Ryan Hembrey joined the band. He'd posted a bunch of flyers around the city advertising for bass lessons, but Kim was the only one who'd called. The band toured to support the album and eventually earned licensing deals with Truckstop/Atavistic and Glitterhouse, an independent European label. In 1997, they returned to their attic studio to record the EP No Breath In the Bellows, which was followed by the full-length Rigging the Toplights a year later.

Pinetop Seven's minimalist mixture of country, jazz, rock and folk music makes them difficult to label. The trio has been backed by various musicians and uses a range of instruments including upright bass, accordion, banjo, mandolin, and slide guitars. ~ Tracy Frey, Rovi